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Table 1 Substrate scope of Mannich bases synthesis

From: Single-step synthesis of a new series of meso di-Mannich bases from the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane and p-substituted phenols

Entry Compound R Product m.p. (°C) [ α ] D 20
c = 0.6, CH2Cl2
Yield (%)
1 7a F 8a 168-169 +5.2 20
2 7b Cl 8b 189-190 +5.7 34
3 7c Br 8c 183-184 +6.0 41
4 7d I 8d 175-177 +7.1 20
5 7e COOMe 8e 128-130 +6.3 17
6 7f COOEt 8f 151-153 +6.8 19
7 7 g COOPr 8 g 118-119 +5.5 18
8 7 h COOBu 8 h 127-129 +4.9 19
9 7i H 8i 146-148 +6.8 20
10 7j Me 8j 162-163 +7.2 46
11 7 k t-Bu 8 k 141-143 +6.3 49
12 7 l OMe 8 l 132-134 +5.9 45
  1. Table 1 shows melting points and yield for each new compound, indicating the p-substituent in aromatic rings in both phenols and compounds 8a-l.